US3686249A - Method of preparing aluminum complexes of polyhydroxy compounds - Google Patents
Method of preparing aluminum complexes of polyhydroxy compounds Download PDFInfo
- Publication number
- US3686249A US3686249A US31749A US3686249DA US3686249A US 3686249 A US3686249 A US 3686249A US 31749 A US31749 A US 31749A US 3686249D A US3686249D A US 3686249DA US 3686249 A US3686249 A US 3686249A
- Authority
- US
- United States
- Prior art keywords
- aluminum
- grams
- sorbitol
- polyhydroxy compound
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 41
- 238000000034 method Methods 0.000 title description 19
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 title description 5
- 229910052782 aluminium Inorganic materials 0.000 abstract description 48
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract description 21
- 239000000600 sorbitol Substances 0.000 abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- -1 ALUMINUM ALKOXIDE Chemical class 0.000 abstract description 12
- 238000001035 drying Methods 0.000 abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 125000004429 atom Chemical group 0.000 description 21
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 10
- 150000004703 alkoxides Chemical group 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 239000004386 Erythritol Substances 0.000 description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 3
- 235000019414 erythritol Nutrition 0.000 description 3
- 229940009714 erythritol Drugs 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 2
- 229940069428 antacid Drugs 0.000 description 2
- 239000003159 antacid agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical class [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- LPJGMJCQLYDIIY-UHFFFAOYSA-N butane-1,1,1-triol propane-1,2,3-triol Chemical class C(CCC)(O)(O)O.OCC(O)CO LPJGMJCQLYDIIY-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical class CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- NKJAFZDLNZQRMZ-UHFFFAOYSA-N hexane-1,1,1,2,2-pentol Chemical class CCCCC(O)(O)C(O)(O)O NKJAFZDLNZQRMZ-UHFFFAOYSA-N 0.000 description 1
- WWYKBCRVBABKLC-UHFFFAOYSA-N hexane-1,1,1,2-tetrol Chemical class CCCCC(O)C(O)(O)O WWYKBCRVBABKLC-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical class CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical class CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- URKBBEIOEBOBIY-UHFFFAOYSA-N pentane-1,1,1,2-tetrol Chemical class CCCC(O)C(O)(O)O URKBBEIOEBOBIY-UHFFFAOYSA-N 0.000 description 1
- FVGBHSIHHXTYTH-UHFFFAOYSA-N pentane-1,1,1-triol Chemical class CCCCC(O)(O)O FVGBHSIHHXTYTH-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical class CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Definitions
- This invention relates to the preparation of aluminum complexes of polyhydroxy compounds. These complexes are useful as antacids and may be used in the same manner as aluminum hydroxide. They are also useful as catalysts in organic reactions where a basic catalyst is used such as in isomerizations, for example, the isomerization of glucose and fructose.
- Aluminum complexes of polyhydroxy compounds are produced by reacting an aluminum alkoxide and a polyhydroxy compound.
- the prior art methods of producing complexes of this general type see, for example, D-avison US. Patent 3,198,332 and Holbert US. Patent 3,352,895) utilize conditions which do not favor complete reaction of the alkoxide groups introduced into the complex by the aluminum alkoxide.
- the presence of residual or partially reacted alkoxide in the complex results in the liberation of alcohol when placed in an acidic environment which can be very undesirable.
- the method of this invention produces virtually completely reacted alkoxide, so that the complex does not release alcohol in an acidic environment. This is accomplished by using a larger quantity of water than was used in prior art methods which promotes the complete reaction of the alkoxide and by the use of a final high vacuum step which strips alcohol from any unreacted alkoxide which is present.
- Aluminum alkoxides are well known and may be prepared, for example, by reacting aluminum with a monohydric alcohol.
- the aluminum alkoxide preferably has the formula Al(OR) where R is alkyl up to C Aluminum isopropoxide is preferred as it is readily available. Mixtures of aluminum alkoxides may also be used.
- the polyhydroxy compound is an organic compound having at least two hydroxyl groups.
- the preferred polyhydroxy compounds which are more readily available, have from 3 to 6 carbon atoms and are linear or branched, preferably linear, and preferably have 2 to 6 3,686,249 Patented Aug. 22, 1972 hydroxyl groups which may be in a vicinal or'in a 1,3- relationship to each other.
- Suitable polyhydroxy compounds include propylene glycol, l,2-, 1,3-, and 2,3-butylene glycols, 1,2-, 1.3-, 2,3, and 2,4-pentylene glycols, 1,2-, 1,3-, 2,3-, and 2,4-hexylene glycols, glycerol butanetriols, pentanetriols, hexanetriols, erythritol, pentanetetrols, hexanetetrols, xylitol, hexanepentols, sorbitol, mannitol, and dulcitol; sorbitol is preferred because it is readily available. Also contemplated are mixtures of polyhydroxy compounds and polymers of polyhydroxy compounds such as hydroxyl bearing polyethers, e.g., diglycerol, polyglycerols, etc.
- the complexes preferably have a ratio of about 0.1 to about 0.7 (preferably about 0.1 to about 0.4) gram atoms of aluminum to each hydroxyl group of the polyhydroxy compound. Ratios outside this range may result in large amounts of unreacted ingredients, polymeric structures, or the dilution of the aluminum to a level where the complex becomes less effective.
- the exact structure of the complex produced is not known. However, it is believed that the product is a mixture of compounds of the following type:
- each R is appropriately selected from hydrogen, alkyl, or hydroxyl-substituted alkyl so that the above compounds result from the reaction of a polyhydroxy compound.
- This amount of water, in moles per gram atom of aluminum is preferably about 6 to about 12 times the number of gram atoms of aluminum chargred divided by the number of hydroxyl equivalents of polyhydroxy compound charged when the ratio of gram atoms of aluminum to each hydroxyl group of the polyhydroxy compound is about 0.1 to about 0.4 and is about 12 to about 18 times the number of gram atoms of aluminum charged divided by the number of hydroxyl equivalents of polyhydroxy compound charged when the ratio of gram atoms of aluminum to each hydroxyl group of the polyhydroxy compound is about 0.4 to about 0.7; this is preferred because the hydroxyl groups on the polyhydroxy compound tend to reduce the need for water.
- the temperature of the reaction is not critical, but about 70 F. is preferred.
- the complex is dried. This is preferably done by vacuum treating under slightly reduced pressure at about 55 to about 90 C.
- drying step removes the excess alcohol, it does not remove the residual alcohol which is attached to the complex in the form of unreacted alkoxide.
- This alcohol is stripped from the complex by vacuum treating underless than about 1 mm. of mercury and. at a temperature of 55 C. to about 90 C. preferably with thorough agitation. (Below 55 C. too much time is required to make the process practical and above 90 C. the complex tends to decompose.)
- Example I being the preferred example:
- Example I A one-liter flask provided with a stirrer and a thermometer was charged with 72.9 grams of sorbitol and 77.1 grams of water and was vigorously stirred and heated to about 35 C. Then 163.2 grams of finely-ground aluminum isopropoxide was added in portions over a 40- minute period during which the temperature rose to 52 C. A thin suspension was formed. After 100 grams of aluminum isopropoxide had been added, the reaction mixture became thicker. Then 180 ml. of isopropyl alcohol was added as a diluent in stages and the reaction was continued at 70 C. for an hour and a half. The product was dried at 50 to 70 C. and 200 mm. for 4 hours and 70 to 80 C. and 20 to 30 mm. for hours.
- Example II Using the same procedure that was used in Example I, a flask was charged with 72.9 grams sorbitol and 136.7 grams water. The solution was stirred vigorously and heated. Then 244.8 grams of finely-ground aluminum isopropoxide was added in portions at 45 to 65 C. As the reaction'proceeded, the mixture became thicker and the temperature reached 70 C. Then 335 ml. isopropyl alcohol was added in stages as a diluent. The reaction was continued at 70 C. for 3% hours. Drying was conducted at 50 to 70 C. and 200 mm. for 4 hours, 70 to 80 C. and 20 mm. for 8 hours. The product was then stripped of combined alcohol at 70 to 80 C. and less than 1 mm. for 48 hours.
- the yield was 138.4 grams and analysis showed 21.4% aluminum, 43.05% ash, 0.27% alcohol, and 0.34% free sorbitol. Approximate molar ratio of aluminum to sorbitol to inorganic hydroxy groups was 3:1:4.9.
- Example III Following the same procedure used in Example I, a flask was charged with 72.9 grams sorbitol and 16.7 grams of water. The mixture was stirred vigorously and heated to 6065 C. Then 81.6 grams finely-ground aluminum isopropoxide was added in portions. The mixture became thicker and reached 70 C. after 22 minutes. The reaction was continued at 70 C. for hours. Drying was then conducted at 50 to 70 C. at 200 mm. for 6 hours. The product was then stripped of combined alcohol at 70 to 80 C. at less than 1 mm. for 8 hours. Theyield was 90.4 grams and analysis showed 12.5% aluminum, 23.7% ash, 0.13% alcohol, and 9.6% free sorbitol. Ap-
- Example IV Using the same procedure used in Example I, the flask was charged with 72.9 grams of sorbitol and 10.2 grams of water. The mixture was vigorously stirred and heated. 81.6 grams of finely-ground aluminum isopropoxide was then added at 65 to 75 C. during 22 minutes. As a diluent 140 ml. isopropyl alcohol was added. The reaction was then continued at 70 C. for 2 hours. The product was dried at 50 to 70 C. at 200 mm. for 2 hours and 70 to C. at 20 mm. for 4 hours. The product was stripped of combined alcohol at 70 to 80 C. at less than 1 mm. for 16 hours. The yield was 88.0 grams. Analysis showed 12.7% aluminum, 24.0% ash, 0.2% alcohol, 6.8% free sorbitol. The approximate molar ratio of aluminum to sorbitol to inorganic hyroxyl groups was l:l:0.64.
- Example V A flask was charged with 72.9 grams sorbitol and 86.2
- Example VI Using the procedure used in Example I, a flask was charged with 72.9 grams sorbitol and 177.2 grams of water. The mixture was vigorously stirred and heated. Then 244.8 grams finely-ground aluminum isopropoxide was added in portions at 60 to 65 C. over a 34-minute period. A diluent of 230 ml. of isopropyl alcohol was then slowly added over a 4-hour period as the reaction was permitted to complete.
- Example VII Erythritol, 122 grams, is mixed with 220 ml. water and heated at 70 C. until dissolved.
- the reaction mixture is heated at 70 C. for about an hour and excess solvent is then removed at that temperature while applying vacuum. Vacuum is gradually increased to below 1 mm. while the solid product is held at about 70 to C. under agitation. Stripping is completed at 70-85 C. and below 1 mm. for about 24 hours.
- the product is a white solid containing 2 gram atoms aluminum per mole of erythritol.
- Example VIII Diglycerol, 166.2 grams, is diluted with 40 ml. water and the solution heated at 70 C.
- Aluminum ethoxide 162.2 grams, is added in portions while the temperature is kept near 70 C.
- Ethanol ml., is added to the reaction mixture when stirring becomes diflicult.
- the reaction temperature is maintained for 15 minutes and then excess alcohol is removed by distillation under slight vacuum. Vacuum is gradually increased to below 1 mm. and stripping of the solid product is carried out at 70-85 C. below 1 mm. for 24 hours.
- the product is a white solid containing 1 gram atom aluminum per mole of diglycerol.
- a process for producing an aluminum complex of a polyhydroxy compound comprising (A) Reacting aluminum alkoxide with a polyhydroxy compound in the presence of an amount of water, in moles per gram atom of aluminum, equal to about 6 to about 18 times the number of gram atoms of aluminum charged divided by the number of hydroxyl equivalents of polyhydroxy compound charged;
- Step (C) Vacuum treating the product formed in Step (B) at about 55 to about 90 C. and at less than about 1 mm. Hg.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3174970A | 1970-04-24 | 1970-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3686249A true US3686249A (en) | 1972-08-22 |
Family
ID=21861190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US31749A Expired - Lifetime US3686249A (en) | 1970-04-24 | 1970-04-24 | Method of preparing aluminum complexes of polyhydroxy compounds |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3686249A (fr) |
| JP (1) | JPS551247B1 (fr) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956352A (en) * | 1973-01-02 | 1976-05-11 | L'oreal | Heterocyclic aluminum compounds and process for their preparation |
| US4284581A (en) * | 1978-10-12 | 1981-08-18 | Ono Pharmaceutical Co., Ltd. | Lithiumaluminium hydride compounds |
| US4336148A (en) * | 1977-09-07 | 1982-06-22 | Ciba-Geigy Corporation | Complex compound, process for their preparation, and their use |
| US4425278A (en) | 1977-09-07 | 1984-01-10 | Ciba-Geigy Corporation | Complex compounds, process for their preparation, and their use |
| US4650888A (en) * | 1984-04-18 | 1987-03-17 | Chugai Seiyaku Kabushiki Kaisha | Pentaerythritol derivative |
| EP0198374A3 (fr) * | 1985-04-12 | 1988-07-20 | Fujian Normal University | Système de couplage d'agents d'aluminium |
| US4766216A (en) * | 1986-11-21 | 1988-08-23 | Warner-Lambert Company | Essentially pure acidic amine ligand aluminum complexes and their preparation |
| US4772724A (en) * | 1986-12-02 | 1988-09-20 | Warner-Lambert Canada Inc. | Essentially pure acid hydroxyl ligand aluminum complexes and their preparation |
| US20030158434A1 (en) * | 2002-01-28 | 2003-08-21 | Pratt Charles E. | Alcohol and glycol modified aluminum tri-alkoxide complexes |
| US20090134369A1 (en) * | 2007-11-26 | 2009-05-28 | Applied Nanoworks, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4974926A (en) * | 1989-04-06 | 1990-12-04 | At&T Bell Laboratories | Underwater optical fiber cable |
-
1970
- 1970-04-24 US US31749A patent/US3686249A/en not_active Expired - Lifetime
-
1971
- 1971-04-24 JP JP2713771A patent/JPS551247B1/ja active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956352A (en) * | 1973-01-02 | 1976-05-11 | L'oreal | Heterocyclic aluminum compounds and process for their preparation |
| US4336148A (en) * | 1977-09-07 | 1982-06-22 | Ciba-Geigy Corporation | Complex compound, process for their preparation, and their use |
| US4425278A (en) | 1977-09-07 | 1984-01-10 | Ciba-Geigy Corporation | Complex compounds, process for their preparation, and their use |
| US4284581A (en) * | 1978-10-12 | 1981-08-18 | Ono Pharmaceutical Co., Ltd. | Lithiumaluminium hydride compounds |
| US4650888A (en) * | 1984-04-18 | 1987-03-17 | Chugai Seiyaku Kabushiki Kaisha | Pentaerythritol derivative |
| EP0198374A3 (fr) * | 1985-04-12 | 1988-07-20 | Fujian Normal University | Système de couplage d'agents d'aluminium |
| US4766216A (en) * | 1986-11-21 | 1988-08-23 | Warner-Lambert Company | Essentially pure acidic amine ligand aluminum complexes and their preparation |
| US4772724A (en) * | 1986-12-02 | 1988-09-20 | Warner-Lambert Canada Inc. | Essentially pure acid hydroxyl ligand aluminum complexes and their preparation |
| US20030158434A1 (en) * | 2002-01-28 | 2003-08-21 | Pratt Charles E. | Alcohol and glycol modified aluminum tri-alkoxide complexes |
| US6953863B2 (en) | 2002-01-28 | 2005-10-11 | Fedchem L.L.C. | Alcohol and glycol modified aluminum tri-alkoxide complexes |
| US20090134369A1 (en) * | 2007-11-26 | 2009-05-28 | Applied Nanoworks, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
| US20100179339A1 (en) * | 2007-11-26 | 2010-07-15 | Auterra, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
| US20100178220A1 (en) * | 2007-11-26 | 2010-07-15 | Auterra, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
| US20100178218A1 (en) * | 2007-11-26 | 2010-07-15 | Auterra, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
| US8262867B2 (en) | 2007-11-26 | 2012-09-11 | Auterra, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
| US8877131B2 (en) | 2007-11-26 | 2014-11-04 | Auterra, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
| US9028768B2 (en) | 2007-11-26 | 2015-05-12 | Auterra, Inc. | Metal alkoxides, apparatus for manufacturing metal alkoxides, related methods and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS551247B1 (fr) | 1980-01-12 |
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